홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

(Pyridin-4-yl)boronic acid → 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (2-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide

HRID 1802252
노트
인쇄 미리보기

반응식

HRID 1802252 반응식
[N:1]1([C:5]([C:7]2[CH:8]=[N:9][N:10]([CH3:25])[C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[C:22](Br)[N:23]=[C:17]3[CH:16]=2)=[O:13])=[O:6])[CH2:4][CH2:3][CH2:2]1.[N:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[N:26]1[CH:31]=[CH:30][C:29]([C:22]2[N:23]=[C:17]3[CH:16]=[C:15]([NH:14][C:12]([C:11]4[N:10]([CH3:25])[N:9]=[CH:8][C:7]=4[C:5]([N:1]4[CH2:4][CH2:3][CH2:2]4)=[O:6])=[O:13])[CH:20]=[CH:19][N:18]3[N:21]=2)=[CH:28][CH:27]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 573782924-(azetidine-1-carbonyl)-N-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide

생성물 1

HCID 573783874-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (2-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide수율 18.8%

시약·촉매·용매 3

HCID 178479796
1,1'-bis(diphenylphosphino)ferrocene palladium (II) chloride dppf
촉매
HCID 10340Sodium Carbonate용매
HCID 312751,4-Dioxane용매

실험 절차

Through a mixture of 4-(azetidine-1-carbonyl)-N-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide (150 mg, 371 μmol) and pyridin-4-ylboronic acid (68.4 mg, 557 μmol) in dioxane (4 ml) and sat. sodium carbonate solution (1 ml) was bubbled nitrogen for 10 minutes, then 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride/dppf (15.2 mg, 18.6 μmol) was added and the resulting mixture was refluxed for 18 hours under nitrogen atmosphere. The solvent was evaporated and the residue was diluted with ethyl acetate and washed with water, the organic layer was separated, dried over magnesium sulfate, filtrated and evaporated. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using ethyl acetate/methanol 2-5% as eluent affording 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (2-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide (28 mg, 18.8%) as a white solid. mp: >250° C., MS: m/z=403.0 (M+H+)

후처리

  1. customwas bubbled nitrogen for 10 minutes
  2. temperaturethe resulting mixture was refluxed for 18 hours under nitrogen atmosphere
  3. customThe solvent was evaporated
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with water
  6. customthe organic layer was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltrated
  9. customevaporated
  10. custompurified by flash chromatography over a 20 g silicagel column

출처 및 근거

ORD 기록
ord-0e0ffa42823a4b31964b185f8ccbb63c
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08349824B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트